Water → HCID 9968539, compound

HRID 428723Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])/[C:6]/2=[CH:13]\[C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1)#[CH:2].I[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.O>CN(C)C=O.C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])/[C:6]/3=[CH:13]\[C:14]2[NH:15][CH:16]=[CH:17][CH:18]=2)=[CH:21][CH:22]=1)([O-:28])=[O:27]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of (Z)-1,3-dihydro-5-ethynyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (150 mg, 0.64 mmol) (from Example 82) and 1-iodo-4-nitrobenzene (175 mg, 0.70 mmol) (Aldrich) in N,N-dimethylformamide (3 mL) (Fisher Scientific) and triethylamine (3 mL) was degassed by bubbling argon through the solution for 15 minutes. Copper(I) iodide (13 mg, 0.068 mmol) (Aldrich) and (Ph3P)2PdCl2 (22 mg, 0.031 mmol) (Aldrich) were added, and the reaction mixture was heated at 70° C. for 13 hours. Water (15 mL) was then added and the precipitate was filtered off and dried. The product was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane to give (Z)-1,3-dihydro-5-(4-nitrophenyl)ethynyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a red powder. (Yield 111 mg, 49%).

Workup

customby bubbling argon through the solution for 15 minutes
filtrationthe precipitate was filtered off
customdried
customThe product was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane

Sources & evidence

ORD record: ord-2ed67f99319f4b419a926cb4961ae414
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313310B1

Reaction notes

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